Study of physicochemical interaction of aryloxyaminopropanol derivatives with teicoplanin and vancomycin phases in view of quantitative structure–property relationship studies

Boronová, Katarína; Lehotay, J.; Hroboňová, Katarína; Armstrong, Daniel W.

doi:10.1016/j.chroma.2013.05.046

Cited by 7 publications

(4 citation statements)

References 17 publications

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“…43,44 The complex structure of macromolecule would provide diverse binding sites, resulting in multiple retention mechanisms. 43,44 The complex structure of macromolecule would provide diverse binding sites, resulting in multiple retention mechanisms.…”

Section: Analysis and Prediction Of Chromatographic Retentionmentioning

confidence: 99%

“…The multiple adsorption mechanisms, such as hydrogenbond, dipole-dipole interaction, π-π interaction, electrostatic interaction, and steric hindrance, have been reported for the enantioseparation of chiral compounds on vancomycin stationary phase. 43,44 The complex structure of macromolecule would provide diverse binding sites, resulting in multiple retention mechanisms. In the view of the three-dimensional structure of vancomycin obtained from the RCSB Protein Data Bank (http:// www.rcsb.org/) database, the molecule of vancomycin was assumed to comprise two adsorption active domains for the interaction with analyes, 45 as shown in Figure 7.…”

Section: Analysis and Prediction Of Chromatographic Retentionmentioning

confidence: 99%

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Enantioseparation of chiral pharmaceuticals by vancomycin‐bonded stationary phase and analysis of chiral recognition mechanism

Liu

Wang

et al. 2019

Chirality

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The drug chirality is attracting increasing attention because of different biological activities, metabolic pathways, and toxicities of chiral enantiomers.The chiral separation has been a great challenge. Optimized high-performance liquid chromatography (HPLC) methods based on vancomycin chiral stationary phase (CSP) were developed for the enantioseparation of propranolol, atenolol, metoprolol, venlafaxine, fluoxetine, and amlodipine. The retention and enantioseparation properties of these analytes were investigated in the variety of mobile phase additives, flow rate, and column temperature. As a result, the optimal chromatographic condition was achieved using methanol as a main mobile phase with triethylamine (TEA) and glacial acetic acid (HOAc) added as modifiers in a volume ratio of 0.01% at a flow rate of 0.3 mL/minute and at a column temperature of 5°C. The thermodynamic parameters (eg, ΔH, ΔΔH, and ΔΔS) from linear van 't Hoff plots revealed that the retention of investigated pharmaceuticals on vancomycin CSP was an exothermic process. The nonlinear behavior of lnk′ against 1/T for propranolol, atenolol, and metoprolol suggested the presence of multiple binding mechanisms for these analytes on CSP with variation of temperature. The simulated interaction processes between vancomycin and pharmaceutical enantiomers using molecular docking technique and binding energy calculations indicated that the calculated magnitudes of steady combination energy (ΔG) coincided with experimental elution order for most of these enantiomers.

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Section: Analysis and Prediction Of Chromatographic Retentionmentioning

confidence: 99%

Section: Analysis and Prediction Of Chromatographic Retentionmentioning

confidence: 99%

Enantioseparation of chiral pharmaceuticals by vancomycin‐bonded stationary phase and analysis of chiral recognition mechanism

Liu

Wang

et al. 2019

Chirality

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“…However, due to the inner complexity of ANN, it is difficult to extract information on how models work to predict the output from input variables. Of notable interest is the use of ANNs to model quantitative retention-structure relationships. − In chiral liquid chromatography, ANNs have been used to predict enantioselective parameters using different CSPs. ,− Our research group, for the first time, used ANN to quantitatively estimate the enantioresolution ( R s ) of a heterogeneous set of chiral molecules …”

Section: Introductionmentioning

confidence: 99%

“… 25 − 28 In chiral liquid chromatography, ANNs have been used to predict enantioselective parameters using different CSPs. 23 , 29 − 34 Our research group, for the first time, used ANN to quantitatively estimate the enantioresolution ( R s ) of a heterogeneous set of chiral molecules. 32 …”

Section: Introductionmentioning

confidence: 99%

Intelligent Recommendation Systems Powered by Consensus Neural Networks: The Ultimate Solution for Finding Suitable Chiral Chromatographic Systems?

Sagrado,

Pardo-Cortina,

Escuder-Gilabert

et al. 2024

Anal. Chem.

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The selection of suitable combinations of chiral stationary phases (CSPs) and mobile phases (MPs) for the enantioresolution of chiral compounds is a complex issue that often requires considerable experimental effort and can lead to significant waste. Linking the structure of a chiral compound to a CSP/MP system suitable for its enantioseparation can be an effective solution to this problem. In this study, we evaluate algorithmic tools for this purpose. Our proposed consensus model, which uses multiple optimized artificial neural networks (ANNs), shows potential as an intelligent recommendation system (IRS) for ranking chromatographic systems suitable for the enantioresolution of chiral compounds with different molecular structures. To evaluate the IRS potential in a proof-of-concept stage, 56 structural descriptors for 56 structurally unrelated chiral compounds across 14 different families are considered. Chromatographic systems under study comprise 7 cellulose and amylose derivative CSPs and acetonitrile or methanol aqueous MPs (14 chromatographic systems in all). The ANNs are optimized using a fit-for-purpose version of the chaotic neural network algorithm with competitive learning (CCLNNA), a novel approach not previously applied in the chemical domain. CCLNNA is adapted to define the inner ANN complexity and perform feature selection of the structural descriptors. A customized target function evaluates the correctness of recommending the appropriate CSP/MP system. The ANN-consensus model exhibits no advisory failures and requires only an experimental attempt to verify the IRS recommendation for complete enantioresolution. This outstanding performance highlights its potential to effectively resolve this problem.

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High-Performance Liquid Chromatography Enantioseparations Using Macrocyclic Glycopeptide-Based Chiral Stationary Phases: An Overview

Ilisz

Orosz

Péter

2019

Methods in Molecular Biology

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Study of physicochemical interaction of aryloxyaminopropanol derivatives with teicoplanin and vancomycin phases in view of quantitative structure–property relationship studies

Cited by 7 publications

References 17 publications

Enantioseparation of chiral pharmaceuticals by vancomycin‐bonded stationary phase and analysis of chiral recognition mechanism

Enantioseparation of chiral pharmaceuticals by vancomycin‐bonded stationary phase and analysis of chiral recognition mechanism

Intelligent Recommendation Systems Powered by Consensus Neural Networks: The Ultimate Solution for Finding Suitable Chiral Chromatographic Systems?

High-Performance Liquid Chromatography Enantioseparations Using Macrocyclic Glycopeptide-Based Chiral Stationary Phases: An Overview

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